Triphenylphosphine → HCID 10482119, compound

HRID 1611713Notes

Reaction equation

HRID 1611713 reaction equation
CCOC(/N=N/C(OCC)=O)=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[NH2:32][C:33]1[N:38]=[C:37]([NH:39][CH2:40][CH2:41][NH:42][C:43]2[CH:48]=[CH:47][C:46]([NH:49][C:50](=O)[CH2:51][N:52]([CH2:54][CH2:55][OH:56])[CH3:53])=[C:45]([C:58]3[CH:63]=[CH:62][C:61]([Cl:64])=[CH:60][C:59]=3[Cl:65])[CH:44]=2)[CH:36]=[CH:35][C:34]=1[N+:66]([O-:68])=[O:67]>C1COCC1>[NH2:32][C:33]1[N:38]=[C:37]([NH:39][CH2:40][CH2:41][NH:42][C:43]2[CH:48]=[CH:47][C:46]([N:49]3[CH2:50][CH2:51][N:52]([CH3:53])[CH2:54][C:55]3=[O:56])=[C:45]([C:58]3[CH:63]=[CH:62][C:61]([Cl:64])=[CH:60][C:59]=3[Cl:65])[CH:44]=2)[CH:36]=[CH:35][C:34]=1[N+:66]([O-:68])=[O:67]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 22254156HCID 22254156, compound

Product 1

HCID 10482119HCID 10482119, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

DEAD (2.5 eq) and PPh3 (2 eq) were added to N-[4-({2-[(6-amino-5-nitro(2-pyridyl))amino]ethyl}amino)-2-(2,4-dichlorophenyl)phenyl]-2-[(2-hydroxyethyl)-methylamino]acetamide (1 eq) dissolved in THF at room temperature. The reaction was heated to 55° C. for 1 hour until completion was determined by LC/MS. The reaction was concentrated and purified by silica column chromatography, eluting with MeOH in CH2Cl2 (5:95, v/v). After collecting the purified fractions and concentrating, 1-[5-({2-[(6-amino-5-nitropyridin-2-yl)amino]ethyl}amino)-2′,4′-dichloro-1,1′-biphenyl-2-yl]-4-methylpiperazin-2-one was attained as a light yellow glass (LC/MS m/z 531.4 MH+) in quantitative yields.

Workup

  1. concentrationThe reaction was concentrated
  2. custompurified by silica column chromatography
  3. washeluting with MeOH in CH2Cl2 (5:95
  4. customAfter collecting the purified fractions
  5. concentrationconcentrating

Sources & evidence

ORD record
ord-a1beb9020d7e48d9a0a35daa2df14f90
Source dataset
uspto-grants-2006_01
Patent number
US06989382B2

Reaction notes

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